US4292232A - Process for the mass coloration of thermoplastics with anthraquinonylaminotraizines - Google Patents
Process for the mass coloration of thermoplastics with anthraquinonylaminotraizines Download PDFInfo
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- US4292232A US4292232A US06/093,644 US9364479A US4292232A US 4292232 A US4292232 A US 4292232A US 9364479 A US9364479 A US 9364479A US 4292232 A US4292232 A US 4292232A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/516—N-acylated derivatives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/547—Anthraquinones with aromatic ether groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/56—Mercapto-anthraquinones
- C09B1/58—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals
- C09B1/585—Mercapto-anthraquinones with mercapto groups substituted by aliphatic, cycloaliphatic, araliphatic or aryl radicals substituted by aryl radicals
Definitions
- Suitable linear polyesters are in particular those which are obtained by polycondensation of terephthalic acid or an ester thereof with a glycol of the formula HO--(CH 2 ) n --OH, in which n is an integer from 2 to 10, or with 1,4-di(hydroxymethyl)cyclohexane, or by polycondensation of a glycol ether of a hydroxybenzoic acid, for example p-( ⁇ -hydroxyethoxy)-benzoic acid.
- the term "linear polyesters” also comprises copolyesters which are obtained by partial replacement of terephthalic acid by another dicarboxylic acid or by a hydroxycarboxylic acid and/or by partial replacement of the glycol by another diol.
- the preferred linear polyester are polyethylene terephthalates.
- the colouration obtained, especially in polyester, are distinguished by good fastness to light, washing, dry cleaning, cross-dyeing, thermofixation, bleeding and chlorite bleaching, as well as by clear shades and good colour strength.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coloring (AREA)
Abstract
A process for the mass coloration of thermoplastics with anthraquinonylaminotriazines of the formula ##STR1## wherein each of X1 and X2 is an alkylmercapto or arylmercapto group or a group of the formula --NR1 R2, in which each of R1 and R2 is alkyl, cycloalkyl, aralkyl or aryl, and R2 can additionally be hydrogen, or R1 and R2 together with the nitrogen atom to which they are attached and optionally a further heteroatom form a 5- or 6-membered ring, one Y is a hydrogen or chlorine atom, a hydroxy, arylmercapto, alkanoylamino or aroylamino group, or a group of the formula ##STR2## and the other Ys are hydrogen atoms, Hal is a chlorine or bromine atom, and n is 0 or 1. Yellow to orange colored fibres of clear shade, good color strength and fastness properties are obtained.
Description
The present invention relates to a process for the mass colouration of thermoplastics with anthraquinonylaminotriazines of the formula ##STR3## wherein each of X1 and X2 is an alkylmercapto or arylmercapto group or a group of the formula --NR1 R2, in which each of R1 and R2 is alkyl, cycloalkyl, aralkyl or aryl, and R2 can additionally be hydrogen, or R1 and R2 together with the nitrogen atom to which they are attached and optionally a further heteroatom form a 5- or 6-membered ring, one Y is a hydrogen or chlorine atom, a hydroxy, arylmercapto, alkanoylamino or aroylamino group, or a group of the formula ##STR4## and the other Ys are hydrogen atoms, Hal is a chlorine or bromine atom, and n is 0 or 1.
Alkylmercapto groups represented by X1 and X2 in formula (1) are preferably those containing 1 to 6 carbon atoms. Suitable arylmercapto groups are e.g. naphthylmercapto groups and, in particular, phenylmercapto groups which are unsubstituted or substituted by chlorine atoms or alkyl or alkoxy groups, each of 1 to 6 carbon atoms. Where X1 and X2 are groups of the formula --NR1 R2, the preferred meanings of R1 and R2 are alkyl groups of 1 to 20 carbon atoms, alkoxyalkyl groups, cycloalkyl groups of 5 to 10 carbon atoms, benzyl or phenylethyl groups, or phenyl groups which are unsubstituted or substituted by chlorine atoms or alkyl or alkoxy groups, each of 1 to 6 carbon atoms, while R2 can additionally be hydrogen.
The two radicals R1 and R2 together with the nitrogen atom to which they are attached can also form e.g. a piperidine or morpholine ring.
An arylmercapto group Y is preferably a phenylmercapto group which can be substituted by chlorine atoms or alkyl or alkoxy groups, each of 1 to 6 carbon atoms. Y can also be an alkanoylamino group of 2 to 6 carbon atoms or a benzoylamino group which is unsubstituted or substituted by chlorine atoms or alkyl or alkoxy atoms of 1 to 6 carbon atoms, but is in particular a hydrogen atom or a OH group. n is preferably 0.
The anthraquinonylaminotriazine compounds to be used in accordance with the invention are known compounds. They are advantageously obtained by condensation of a chlorotriazine of the formula ##STR5## with the corresponding aminoanthraquinone, for example 1-aminoanthraquinone, 1-aminoanthraquinone-3-, -4-, -5-, -6- or -7-chloroanthraquinone, 1-aminoanthraquinone-4-hydroxyanthraquinone, 1-aminoanthraquinone-4-, -5- or -8-phenylmercaptoanthraquinone, 1-aminoanthraquinone-4- or -5-acetylaminoanthraquinone, 1-aminoanthraquinone-4- or -5-benzoylaminoanthraquinone.
The triazines of the formula (2) are obtained by the stepwise replacement of two chlorine atoms in cyanuric chloride by the amines or mercaptans X1 H and X2 H.
The following amines are cited as examples: methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, n-hexylamine, n-octylamine, n-decylamine, n-dodecylamine, n-hexadecylamine, or n-octadecylamine, dimethylamine, diethylamine, di-n-propylamine or di-n-butylamine, β-methoxyethylamine, γ-methoxy-n-propylamine or γ-isopropoxy-n-propylamine, cyclohexylamine, dicyclohexylamine, benzylamine, phenylethylamine, aniline, o-, m- or p-toluidine, N-methylaniline, N-ethylaniline or N-n-butylaniline, 1-aminonaphthalene, piperidine or morpholine.
Table I lists a number of anthraquinonylaminotriazines of the formula ##STR6## wherein A is the 1-anthraquinonyl radical, m is 1, and the meanings of X1 and X2 are indicated in columns II and III.
TABLE I
______________________________________
No. X.sub.1 X.sub.2
______________________________________
1 β-methoxyethylamino
β-methoxyethylamino
2 γ-methoxypropylamino
γ-methoxypropylamino
3 γ-isopropoxypropylamino
γ-isopropoxypropylamino
4 benzylamino benzylamino
5 phenylethylamino phenylethylamino
6 n-hexadecylamino n-hexadecylamino
7 n-octadecylamino n-octadecylamino
8 methylamino ethylamino
9 methylamino n-butylamino
10 methylamino n-hexadecylamino
11 ethylamino n-octadecylamino
12 methylamino dimethylamino
13 methylamino diethylamino
14 methylamino di-n-propylamino
15 methylamino di-n-butylamino
16 ethylamino dimethylamino
17 methylamino anilino
18 ethylamino anilino
19 isopropylamino anilino
20 n-butylamino anilino
21 n-hexadecylamino anilino
22 n-octadecylamino anilino
23 methylamino N-methyl-anilino
24 ethylamino N-methyl-anilino
25 dimethylamino diethylamino
26 dimethylamino diisopropylamino
27 dimethylamino di-n-butylamino
28 dimethylamino N-methyl-anilino
29 di-isopropylamino N-methyl-anilino
30 di-n-butylamino N-methyl-anilino
31 anilino N-methyl-anilino
32 N-methyl-anilino N-ethyl-anilino
34 ethylmercapto methylmercapto
35 ethylmercapto n-propylmercapto
36 ethylmercapto n-butylmercapto
37 ethylmercapto n-hexadecylmercapto
38 ethylmercapto n-octadecylmercapto
39 methylmercapto phenylmercapto
40 ethylmercapto phenylmercapto
41 anilino phenylmercapto
42 N-methylanilino phenylmercapto
43 N-ethylanilino phenylmercapto
44 methylamino methylmercapto
45 methylamino ethylmercapto
46 methylamino n-propylmercapto
47 methylamino n-butylmercapto
48 methylamino n-hexadecylmercapto
49 methylamino n-octadecylmercapto
50 ethylamino methylmercapto
51 diethylamino methylmercapto
52 dimethylamino methylmercapto
53 dimethylamino ethylmercapto
54 diethylamino ethylmercapto
55 di-n-butylamino ethylmercapto
56 dimethyamino n-propylmercapto
57 anilino methylmercapto
58 anilino ethylmercapto
59 anilino n-propylmercapto
60 anilino n-butylmercapto
61 anilino n-hexadecylmercapto
62 anilino n-octadecylmercapto
63 N-methylanilino methylmercapto
64 N-ethylanilino methylmercapto
______________________________________
Table II lists further anthraquinonylaminotriazines of the formula (3), wherein m is 2, A is the anthraquinone radical which is bonded to the triazinylamino groups in the positions indicated in column II, and X1 and X2 have the meanings given in columns III and IV.
TABLE II
______________________________________
Posi-
No. tion X.sub.1 X.sub.2
______________________________________
65 1,4 β-methoxyethylamino
β-methoxyethylamino
66 1,5 β-methoxyethylamino
β-methoxyethylamino
67 1,4 γ-methoxypropylamino
γ-methoxypropylamino
68 1,5 γ-methoxypropylamino
γ-methoxypropylamino
69 1,4 γ-isopropoxypropyl-
γ-isopropxypropylamino
amino
70 1,5 γ-isopropoxypropyl-
γ-isopropxypropylamino
amino
71 1,4 benzylamino benzylamino
72 1,5 benzylamino benzylamino
73 1,4 n-hexadecylamino
n-hexadecylamino
74 1,5 n-hexadecylamino
n-hexadecylamino
75 1,4 methylamino methylamino
76 1,5 methylamino methylamino
77 1,4 butylamino butylamino
78 1,5 butylamino butylamino
79 1,4 dimethylamino dimethylamino
80 1,5 dimethylamino dimethylamino
81 1,4 morpholyl morpholyl
82 1,5 morpholyl morpholyl
83 1,4 anilino anilino
84 1,5 anilino anilino
85 1,4 phenylmercapto phenylmercapto
86 1,5 phenylmercapto phenylmercapto
87 1,4 n-butylmercapto n-butylmercapto
88 1,5 n-butylmercapto n-butylmercapto
89 1,4 n-hexadecylmercapto
n-hexadecylmercapto
90 1,5 n-hexadecylmercapto
n-octadecylmercapto
91 1,4 n-octadecylmercapto
n-octadecylmercapto
92 1,5 n-octadecylmercapto
n-octadecylmercapto
93 1,4 methylamino anilino
94 1,5 methylamino anilino
95 1,4 methylamino N-methylanilino
96 1,5 methylamino N-methylanilino
97 1,4 dimethylamino anilino
98 1,5 dimethylamino anilino
99 1,4 methylmercapto anilino
100 1,5 methylmercapto anilino
101 1,4 methylmercapto N-methylanilino
102 1,5 methylmercapto N-methylanilino
103 1,4 n-butylmercapto anilino
104 1,5 n-butylmercapto anilino
105 1,4 n-octadecylmercapto
anilino
106 1,5 n-octadecylmercapto
anilino
107 1,4 methylmercapto phenylmercapto
108 1,5 methylmercapto phenylmercapto
109 1,4 n-butylmercapto phenylmercapto
110 1,5 n-butylmercapto phenylmercapto
111 1,4 methylmercapto n-hexadecylmercapto
112 1,5 methylmercapto n-hexadecylmercapto
113 1,4 methylamino dimethylamino
114 1,5 methylamino dimethylamino
115 1,4 methylmercapto morpholinyl
116 1,5 methylmercapto morpholinyl
117 1,4 n-hexadecylamino
anilino
118 1,5 n-hexadecylamino
anilino
119 1,4 isopropylamino anilino
120 1,5 isopropylamino anilino
121 1,4 anilino N-methylanilino
122 1,5 anilino N-methylanilino
123 1,4 methylamino methylmercapto
124 1,5 methylamino methylmercapto
125 1,4 dimethylamino methylamino
126 1,5 dimetylamino methylamino
127 1,4 dimethylamino methylmercapto
128 1,5 dimethylamino methylmercapto
129 1,5 ethylamino butylamino
______________________________________
Table III lists compounds of the formula ##STR7## wherein X1 and X2 have the meanings given in columns II and III and Y is as defined in column IV. Column V indicates the position of Y.
TABLE III
______________________________________
No. X.sub.1 X.sub.2 Y Position
______________________________________
130 ethylamino butylamino hydroxy 4
131 cyclohexyl-
cyclohexyl-
hydroxy 4
amino amino
132 dimethyl- dimethyl- 2,4-bisanilino-
4
amino amino triazinyl-6-
amino
133 N-methyl- phenylamino
2,4-bisethyl-
4
anilino aminotriazinyl-
6-amino
134 N-methyl- phenylamino
2,4-bisethyl-
5
anilino aminotriazinyl-
6-amino
135 N-methyl- phenylamino
2,4-bisphenyl-
4
anilino mercapto-tria-
zinyl-6-amino
______________________________________
It is also possible to use mixtures of different dyes.
Examples of thermoplastics are polyolefins, such as polyethylene, polypropylene or polyisobutylene, also polyvinyl chloride, polystyrene, as well as copolymers of styrene, such as ABS, and especially linear polyesters.
Suitable linear polyesters are in particular those which are obtained by polycondensation of terephthalic acid or an ester thereof with a glycol of the formula HO--(CH2)n --OH, in which n is an integer from 2 to 10, or with 1,4-di(hydroxymethyl)cyclohexane, or by polycondensation of a glycol ether of a hydroxybenzoic acid, for example p-(β-hydroxyethoxy)-benzoic acid. The term "linear polyesters" also comprises copolyesters which are obtained by partial replacement of terephthalic acid by another dicarboxylic acid or by a hydroxycarboxylic acid and/or by partial replacement of the glycol by another diol. However the preferred linear polyester are polyethylene terephthalates.
Colouration is effected by the conventional methods, for example by mixing the colourants with the plastics material in granulate or particulate form and extruding the mixture to fibres, sheets or granules. These latter can then be moulded to objects by injection moulding.
The colouration obtained, especially in polyester, are distinguished by good fastness to light, washing, dry cleaning, cross-dyeing, thermofixation, bleeding and chlorite bleaching, as well as by clear shades and good colour strength.
Russian Pat. No. 192.993 and German Auslegeschrift No. 1 644 532 describe anthraquinone dyes which in the 4-position contain an arylamino group. In contradistinction thereto, the colourants employed in the present invention colour polyester in shades of distinctly better fastness to light and resistance to atmospheric influences.
The invention is illustrated by the following Examples, in which parts and percentages are by weight.
A non-delustred polyethylene terephthalate granulate suitable for fibre manufacture is shaken in a closed vessel for 15 minutes on a mechanical shaker together with 1% of 1-(2',4'-bis-N-methyl-N-phenylamino-1',3',5'-triazinyl-6')-aminoanthraquinone. The uniformly coloured granules are then spun in a melt spinning machine (285° C.±3° C., sojourn time in the spinning machine about 5 minutes) to filaments, which are stretched and wound on a draw twister. The solubility of the colourant in polyethylene terephthalate results in a strong yellow colouration which is distinguished by outstanding light-fastness, excellent fastness to washing, dry cleaning, cross-dyeing, sublimation and rubbing after thermofixation, and also by excellent resistance to chlorite bleaching and good viscosity values.
1000 parts of polyethylene terephthalate granules, 10 parts of titanium oxide (Kronos RN 40) and 1 part of finely divided 1-(2',4'-bis-N-methyl-N-phenylamino-1',3',5'-triazinyl-6')-amino-4-hydroxyanthraquinone are mixed in a closed vessel for 2 hours on a roller gear table. The coloured granules are extruded at about 260° C. to strands of 2 mm, which are re-granulated. The resultant granules are processed at 270°-280° C. in a screw injection moulding machine to mouldings. The red coloration obtained is of very good light-fastness.
Table IV lists further colourants of the formula (3) which were used for colouring polyethylene terephthalate by the methods described in Examples 1 and 2. A is the anthraquinonyl radical. The meanings of X1, X2 and m are indicated in columns II, III and IV respectively. The position of the triazinylamino group in the anthraquinone radical is indicated in column V.
TABLE IV
______________________________________
Exam- Posi-
ple X.sub.1 X.sub.2 m tion Colour
______________________________________
3 methylamino methylamino 1 1 yellow
4 methylamino methylamino 2 1,5 yellowish
orange
5 ethylamino ethylamino 1 1 yellow
6 ethylamino ethylamino 2 1,5 yellowish
orange
7 n-butylamino
n-butylamino
1 1 yellow
8 dimethylamino
dimethylamino
1 1 yellow
9 diethylamino
diethylamino
1 1 yellow
10 diisopropyl-
diisopropyl-
1 1 yellow
amino amino
11 di-n-butyl- di-n-butyl 1 1 yellow
amino amino
12 piperidyl piperidyl 1 1 yellow
13 morpholyl morpholyl 1 1 yellow
14 anilino anilino 1 1 yellow
15 N-methylani-
N-methylani-
1 1 yellow
lino lino
16 N-methylani-
N-methylani-
2 1,4 violet
lino lino
17 N-methylani-
N-methylani-
2 1,5 reddish
lino lino yellow
18 diphenylamino
diphenylamino
1 1 yellow
19 phenylmercapto
phenylmercapto
1 1 yellow
20 methoxypropio-
methoxypropio-
1 1 yellow
nylamino nylamino
21 isopropoxy- isopropoxy- 1 1 yellow
propylamino propylamino
22 methoxyethyl-
methoxyethyl-
1 1 yellow
amino amino
23 amino amino 1 1 yellow
24 benzylamino benzylamino 1 yellow
25 phenylethyl-
phenylethyl-
1 1 yellow
amino amino
26 diisopropyl-
diisopropyl-
2 1,5 orange
amino amino
27 diisopropyl-
phenylmercapto
1 1 yellow
amino
28 diisopropyl-
p-toluidino 1 1 yellow
amino
29 dimethylamino
methylmer- 1 1 yellow
capto
30 methylmer- methylmer- 1 1 yellow
capto capto
31 methylmer- butyl-2-mer-
1 1 yellow
capto capto
32 methylmer- methylmer- 2 1,5 reddish
capto capto yellow
33 N-methyl- N-methyl- 2 1,8 reddish
anilino anilino yellow
34 methylmercapto
anilino 1 1 yellow
35 methylmercapto
phenylmercapto
1 1 greenish
yellow
36 methylmercapto
o-phenetidino
1 1 greenish
yellow
37 methylmercapto
p-phenetidino
1 1 yellow
38 methylmercapto
4-chlorophenyl-
1 1 yellow
mercapto
39 methylmercapto
2,5-dichlor-
1 1 yellow
phenyl
40 methylmercapto
4-methylphenyl
1 1 yellow
41 phenylmercapto
morpholino 1 1 yellow
42 phenylmercapto
cyclohexyl-1-
1 1 yellow
amino
______________________________________
Table IV lists further colourants of the formula (4) which were used to colour polyethylene terephthalate by the methods described in Examples 1 and 2. A is the anthraquinonyl radical. The meanings of X1, X2 and Y are given in columns II, III and IV respectively. Column V indicates the position of Y in the anthraquinonyl radical and column VI the shade of the coloured polyester fibres.
TABLE V
______________________________________
Ex- Po-
am- si-
ple X.sub.1 X.sub.2 Y tion Colour
______________________________________
43 ethylamino ethylamino hydroxy 4 red
44 ethylamino ethylamino benzoyl- 5 reddish
amino yellow
45 anilino anilino hydroxy 4 red
46 N-methyl- N-methyl- hydroxy 4 red
anilino anilino
47 N-methyl- N-methyl- benzoyl- 5 reddish
anilino anilino amino yellow
48 N-methyl- N-methyl- benzoyl- 5 reddish
anilino anilino amino yellow
49 N-methyl- N-methyl- phenylmer-
4 red
anilino anilino capto
50 N-methyl- N-methyl- phenylmer-
5 yellow
anilino anilino capto
51 butylamino butylamino benzoyl- 4 red
amino
52 cyclohexyl-
cyclohexyl-
benzoyl- 4 claret
amino amino amino
53 diethyl- diethyl- benzoyl- 4 red
amino amino amino
54 diisopro- diisopro- hydroxy 4 red
pylamino pylamino
55 methylmer- methylmer- 4-chlorben-
4 red
capto capto zoylamino
56 methylmer- butyl-2- 4-chlorben-
4 red
capto mercapto zoylamino
57 methylmer- dimethyl- phenylmer-
5 yellow
capto amino capto
58 methylamino
methylamino
phenylmer-
5 brown-
capto ish
yellow
59 N-methyl- N-methyl- phenylmer-
5 yellow
anilino anilino mercapto
60 N-methyl- N-methyl- 4-chlorphe-
5 yellow
anilino anilino nylmercapto
61 N-methyl- N-methyl- phenylmer-
8 yellow
anilino anilino capto
62 methylmer- anilino chlorine 3 green-
capto ish
yellow
63 methylmer- 2-chlor- chlorine 3 green-
capto anilino ish
yellow
64 methylmer- 3-chlor- chlorine 3 green-
capto anilino ish
yellow
65 methylmer- anilino chlorine 4 yellow
capto
66 methylmer- o-anisidino
chlorine 4 yellow
capto
67 methylmer- p-anisidino
chlorine 4 yellow
capto
68 methylmer- anilino chlorine 6 yellow
capto
69 methylmer- o-toluidino
chlorine 5 yellow
capto
70 p-toluidino
p-toluidino
chlorine 5 yellow
71 methylmer- anilino chlorine 6(7) yellow
capto
72 methylmer- p-chlorani-
chlorine 6(7) yellow
capto lino
73 methylmer- m-toluidino
chlorine 6(7) yellow
capto
74 dimethyl- dimethyl- 2-chloro-
4 red
amino amino benzoyl-
amino
75 dimethyl- dimethyl- 3-chloro-
4 claret
amino amino benzoyl-
amino
76 dimethyl- dimethyl- 2-fluoro-
4 claret
amino amino benzoyl-
amino
77 dimethyl- dimethyl- acetyl- 4 claret
amino amino amino
78 methylmer- phenylmer- hydroxy 4 red
capto capto
79 methylmer- phenylmer- benzoyl- 4 red
capto capto amino
80 methylmer- phenylmer- benzoyl- 5 yellow
capto capto amino
81 phenylmer- cyclohe- hydroxy 4 red
capto xylamino
82 phenylmer- morpholino hydroxy 4 red
capto
______________________________________
Claims (10)
1. A process for the mass coloration of a thermoplastic in the melt in which the coloration is effected by
incorporating in said thermoplastic in the melt an effective amount of an anthraquinonylaminotriazine of the formula (1) ##STR8## wherein each of X1 and X2 is an alkylmercapto or arylmercapto group or a group of the formula --NR1 R2, in which each of R1 and R2 is alkyl, cycloalkyl, aralkyl or aryl, and R2 can additionally be hydrogen, or R1 and R2 together with the nitrogen atom to which they are attached form a 5- or 6-membered ring or are morpholino, one Y is a hydrogen or chlorine atom, a hydroxy, arylmercapto, alkanoylamino or aroylamino group, or a group of the formula ##STR9## and the other Ys are hydrogen atoms, Hal is a chlorine or bromine atom, and n is 0 or 1.
2. A process according to claim 1, where in the compound of the formula (1), each of X1 and X2 is a group of the formula --NR1 R2, in which R1 and R2 are alkyl groups of 1 to 20 carbon atoms, alkoxyalkyl groups, cycloalkyl groups of 5 to 6 carbon atoms, benzyl or phenylethyl groups or phenyl groups which are unsubstituted or substituted by chlorine atoms, alkyl or alkoxy groups, each of 1 to 6 carbon atoms, and R2 can additionally be hydrogen.
3. A process according to claim 1, where in the compound of the formula (1), X1 is an alkylmercapto group of 1 to 6 carbon atoms or a group of the formula --NR1 R2, in which R1 and R2 are as defined in claim 2 and X2 is an alkylmercapto group of 1 to 6 carbon atoms.
4. A process according to claim 1, where the compound of the formula (1) is ##STR10##
5. A process according to claim 1, where the compound of the formula (1) is ##STR11##
6. A process according to claim 1, where the compound of the formula (1) is ##STR12##
7. A process according to claim 1, where the compound of the formula (1) is ##STR13##
8. A process according to claim 1, where the compound of the formula (1) is ##STR14##
9. A thermoplastic mass colored by the process according to claim 1.
10. A linear polyester mass colored by the process according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1202778 | 1978-11-23 | ||
| CH12027/78 | 1978-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4292232A true US4292232A (en) | 1981-09-29 |
Family
ID=4379160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US06/093,644 Expired - Lifetime US4292232A (en) | 1978-11-23 | 1979-11-13 | Process for the mass coloration of thermoplastics with anthraquinonylaminotraizines |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4292232A (en) |
| EP (1) | EP0012110B1 (en) |
| JP (1) | JPS5573735A (en) |
| CA (1) | CA1142670A (en) |
| DE (1) | DE2966628D1 (en) |
| ES (1) | ES8101676A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4442287A (en) * | 1981-07-10 | 1984-04-10 | Basf Aktiengesellschaft | Anthraquinone dyes |
| US4804719A (en) * | 1988-02-05 | 1989-02-14 | Eastman Kodak Company | Water-dissipatable polyester and polyester-amides containing copolymerized colorants |
| US5730906A (en) * | 1996-07-12 | 1998-03-24 | Exxon Research And Engineering Company | Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60250052A (en) * | 1984-05-28 | 1985-12-10 | Mitsubishi Chem Ind Ltd | Colorant for resin |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163551A (en) * | 1959-05-06 | 1964-12-29 | Ciba Ltd | Process for dyeing high-molecular organic products with pigment dyestuffs |
| US3349089A (en) * | 1964-05-06 | 1967-10-24 | Gnii Orch Produktov I Krasitel | Triazine dyes of the anthraquinone series |
| US3459729A (en) * | 1963-01-15 | 1969-08-05 | Acna | Monoazo triazine containing dyestuffs |
| US4198205A (en) * | 1976-01-21 | 1980-04-15 | Basf Aktiengesellschaft | Triazinyl-anthraquinone dye formulations for cellulose or cellulosic fibrous material |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1191060B (en) * | 1960-06-11 | 1965-04-15 | Cassella Farbwerke Mainkur Ag | Process for the production of pigment dyes |
| DE1644532A1 (en) * | 1964-05-05 | 1969-05-22 | Gnii Orch Poluprodktov I Krasi | Water-insoluble triazine dyes of the anthraquinone series used for dyeing synthetic fibers |
| DE2017504A1 (en) * | 1970-04-13 | 1971-10-28 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Process for the continuous dyeing of synthetic fiber materials |
| GB1373910A (en) * | 1971-12-08 | 1974-11-13 | Yorkshire Chemicals Ltd | Anthraquinone disperse dyes |
-
1979
- 1979-11-13 US US06/093,644 patent/US4292232A/en not_active Expired - Lifetime
- 1979-11-19 DE DE7979810158T patent/DE2966628D1/en not_active Expired
- 1979-11-19 EP EP79810158A patent/EP0012110B1/en not_active Expired
- 1979-11-21 CA CA000340323A patent/CA1142670A/en not_active Expired
- 1979-11-22 JP JP15192479A patent/JPS5573735A/en active Pending
- 1979-11-22 ES ES486239A patent/ES8101676A1/en not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163551A (en) * | 1959-05-06 | 1964-12-29 | Ciba Ltd | Process for dyeing high-molecular organic products with pigment dyestuffs |
| US3459729A (en) * | 1963-01-15 | 1969-08-05 | Acna | Monoazo triazine containing dyestuffs |
| US3349089A (en) * | 1964-05-06 | 1967-10-24 | Gnii Orch Produktov I Krasitel | Triazine dyes of the anthraquinone series |
| US4198205A (en) * | 1976-01-21 | 1980-04-15 | Basf Aktiengesellschaft | Triazinyl-anthraquinone dye formulations for cellulose or cellulosic fibrous material |
Non-Patent Citations (3)
| Title |
|---|
| Chemical Abstracts, vol. 77:5828a; 1972. * |
| Chemical Abstracts, vol. 84:180931v; 1976. * |
| Chemical Abstracts, vol. 85:193386s; 1976. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4442287A (en) * | 1981-07-10 | 1984-04-10 | Basf Aktiengesellschaft | Anthraquinone dyes |
| US4804719A (en) * | 1988-02-05 | 1989-02-14 | Eastman Kodak Company | Water-dissipatable polyester and polyester-amides containing copolymerized colorants |
| US5730906A (en) * | 1996-07-12 | 1998-03-24 | Exxon Research And Engineering Company | Additive combination to reduce deposit forming tendencies and improve antioxidancy of aviation turbine oils (Law406) |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5573735A (en) | 1980-06-03 |
| CA1142670A (en) | 1983-03-08 |
| ES486239A0 (en) | 1980-12-16 |
| EP0012110A1 (en) | 1980-06-11 |
| ES8101676A1 (en) | 1980-12-16 |
| EP0012110B1 (en) | 1984-02-01 |
| DE2966628D1 (en) | 1984-03-08 |
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| AS | Assignment |
Owner name: CIBA-GEIGY CORPORATION, 444 SAW MILL RIVER RD., AR Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:CIBA-GEIGY AG;REEL/FRAME:003827/0842 Effective date: 19810206 |
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| STCF | Information on status: patent grant |
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| AS | Assignment |
Owner name: CIBA SPECIALTY CHEMICALS CORPORATION, NEW YORK Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CIBA-GEIGY CORPORATION;REEL/FRAME:008447/0975 Effective date: 19961227 |